If Portfolia succeeds, it will funnel over $1 billion into startups that women care about by 2022.

Trish Costello, founder and CEO of investing platform Portfolia, holds the giveaway up high, offering the 60-plus conference attendees gathered in this Boston ballroom a chance to take a look. Dubbed vSculpt, the product is a vaginal rejuvenation device designed for women who suffer from low bladder control and other pelvic floor issues, post-childbirth. At any other conference, vSculpt might prompt some awkward throat-clearing (“leakage,” anyone?). But here, in a room full of women angel investors, the crowd lets out a whoop.

Costello knows her audience. After leading the prestigious Kauffman Fellows (a career development program for venture capital investors) for over a decade, she launched Portfolia five years ago with the goal of convincing affluent women to think beyond traditional philanthropy and begin investing in startups. “There are 5 million accredited women [investors] in the U.S.,” she says. “Our goal is to touch every one of them.”

Trish Costello, Portfolia CEO and Founder

But Costello doesn’t want to simply engage more women in investing; she wants to fundamentally change which ideas win venture support. vSculpt, designed and developed by a woman entrepreneur who experienced pelvic floor issues firsthand, embodies that type of product that she believes traditional investors have too long ignored. “This is all about how we shift the world when we put our money behind the solutions that we want to see,” she says.

That message has resonated with hundreds of women. Already, Portfolia has created funds devoted to aging, consumer, enterprise, and women’s health. If it can enlist 100,000 women by 2022, as Costello envisions, then the platform will have helped pump more than $1 billion into startups, such as vSculpt maker Joylux, which serve market needs that women value. (Startups led by men are equally welcome to pitch.)

ANGELS ASCENDANT

Portfolia isn’t alone. A growing number of angel organizations are geared toward women. One of the most prominent, Pipeline Angels, runs bootcamps on topics such as valuations and pro-rata investment rights. Pipeline Angels’ alumnae network includes the founders of 37 Angels and Topstone Angels, both based on the East Coast. On the West Coast, there is #Angels, a group founded by six former Twitter executives in 2015, and Broadway Angels, a group led by women VCs who moonlight as angels. A Harvard study published in 2017 suggests that organizations such as these have helped drive a major bump in angel investing by women. Prior to 2002, 18% of angels were women; since 2014, 30% of new angels are women.

But Portfolia stands apart. Unlike a traditional angel network, in which investors make their own decisions about each pitch and write their own checks, Portfolia functions more like a micro-VC. With a check of between $10,000 and $100,000, women can join an open fund of their choosing. Each fund is spearheaded by a small team of experienced investors, who take the lead in managing deal flow and conducting due diligence (they also earn a larger portion of the fund’s profits). By pooling their money in this way, Portfolia’s members are able to learn from one another and quickly diversify their portfolios. All fund contributors are welcome to participate throughout the investment process, asking questions and offering their own expertise. Along the way, novice investors get a chance to learn from veterans.

“Normally if you’re a limited partner you have no interaction with the investing process at all,” Costello says. “Our view is, LPs can’t make the decisions, but would they want to be engaged? We see investing as a collaborative experience.”

Costello has also designed the funds with flexibility in mind, given the busy and variable schedules of the women she hopes to attract. “You put your money in and you can be as involved or as passive as you like,” she says. “You can source deals, you can watch every month when the companies present, you can vote on them, you can be on a diligence team, you can be on an advisory board. Or you can just read the quarterly report.”

THE PORTFOLIO APPROACH

Rachel Sheinbein, an MIT-trained engineer and venture capitalist, had been angel investing with her husband, making bets on over 50 companies, when she met Costello. While Sheinbein liked the autonomy of traditional angel investing, Costello’s portfolio-based approach intrigued her. “If some don’t go well, which is expected, you have some buffer, because you’re in a portfolio.” At Costello’s prompting, she joined Portfolia’s enterprise fund.

Almost immediately, Sheinbein was struck by the difference between the Portfolia experience and her prior experience as a partner at CMEA Capital, now Presidio Partners, which she left in 2014. “There’s a lot less bravado in the conversations, and there’s a real focus on cooperation,” she says. “It doesn’t mean we all agree or think the same way, but there’s a different kind of energy attached to it.”

The Portfolia Investor Summit: Activating Women’s Health [Photo: courtesy of Portfolia]As the enterprise fund progressed, taking pitches from two or three startups per month, Sheinbein also observed a shift in the confidence of the fund participants who were new to investing. “I see how the women are getting more comfortable, and [realizing] that it is a bit of an art,” she says. “It’s demystifying the language, demystifying the process.”

At Portfolia, the investment process is designed to be readily accessible to fund members regardless of their location. Startups pitch via videoconference, fielding questions from any members who choose to join. After deciding which startups, if any, should advance to due diligence, fund members form smaller teams that tackle the nitty-gritty.

Enterprise fund participant Lolita Taub, who met Costello last summer, had been exposed to the venture capital world while working as VP of sales at a startup. But she hadn’t herself played the role of investor until she joined Portfolia. “Some of the investors have a lot more experience, and you get to hear the questions that are being asked,” she says. “Where I add value is on sales. Can this thing sell? Why, and how? I particularly liked one startup, and I went into the due diligence phase for that one. We didn’t end up investing in it, but that was a great learning experience.”

After a Portfolia fund closes a deal, founding teams get the benefit of fund members’ rich network of contacts. “A lot of the women are pretty prominent and very accomplished. You can tap into their financial capital and their social capital,” says lawyer Lorine Pendleton, a participant in two Portfolia funds. Over Slack, founders share updates and make requests. “Our entrepreneurs will post, ‘Hey, we’re recruiting–do you know anyone in your network?'”

INVESTORS ON CALL

More established investors are discovering the value of the Portfolia network. Earlier this year, VC firm New Enterprise Associates (NEA) was leading a $40 million round in a company that fit Portfolia’s criteria. “All the customers were women. All the investors were men. So, I got a call,” says Costello. NEA invited Portfolia to invest $100,000, offering the same terms that it had negotiated. “‘Bring all your women investors, we really feel like it would make a difference to have that kind of feedback,'” Costello recalls the firm saying. She expects to see further co-invest offers cross her desk, thanks to the relationships she developed while running Kauffman Fellows. “We see things that most people don’t see, and we’re able to add value because of who I’m bringing to the table.”

For veteran VC Nola Masterson, one of the leads for Portfolia’s newly launched “femtech” fund, the opportunity to get introduced into later-stage rounds, an angel-network rarity, sealed the deal on her participation. She also appreciated Portfolia’s “learn by doing” philosophy, which she herself once practiced, in a more ad hoc way, at storied venture firm Kleiner, Perkins, Caufield and Byers, where she served as a consultant. The firm operated a side fund for consultants and advisors, and Masterson took full advantage, her enthusiasm surprising even KPCB’s Brook Byers himself. “The only way to learn is to get involved and put your money where your mouth is,” she says.

During Portfolia’s Boston investor summit in April, the women in attendance are doing just that. They talk about their exasperation with “leaning in” so far that, as one says, “I’m falling over.” They raise the question of how to protest behavior that is hostile to women—for instance, by boycotting the LPs that backed disgraced Binary Capital cofounder Justin Caldbeck. They nod in agreement when one speaker advocates “taking control of the economic power” that happens outside of the public markets.

“How many of you believe that your financial capital can drive change?” Adrienne Penta, executive director of the Brown Brothers Harriman Center for Women and Wealth, asks the attendees. Every hand rises high.

By the time Joanne Wilson, well known for her Gotham Gal blog on angel investing, takes the stage to close out the day, the attendees have begun to refer to Portfolia as a “movement.” From her white leather chair, Wilson dispenses advice on follow-on rounds and knowing your own strengths. She also points to a trend that bodes well for Portfolia.

“Taking money from the big names has peaked,” Wilson says. “Founders are taking money from the investors who understand their businesses.”

In Portfolia, founders may soon find such backers—by the thousands.

Staff writer Ainsley (O'Connell) Harris covers the business of technology with a focus on financial services and education. Follow her on Twitter at @ainsleyoc.

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